Toluene → N-[4-Fluoro-2-[(2-methyl-2-propen-1-yl)oxy]phenyl]acetamide

Participants

Reaction Conditions

Reaction Steps

3-Chloro-2-methylpropene (1.36 g, 15 mmol) was added to a mixture of 5-fluoro-2-nitro-phenol (1.57 g, 10 mmol), potassium carbonate (2.76 g, 20 mmol), tetrabutylammonium hydrogen sulfate (0.068 g, 0.2 mmol) and acetonitrile (30 ml), and the mixture was heated under reflux for 18 h. The cold reaction mixture was diluted with toluene and washed with 5% aqueous potassium carbonate, dried and evaporated. A part of the residue (0.631 g, 3 mmol), sodium dithionite (1.04 g, 6 mmol) in EtOH-THF-H2O (2:1:1, 3 ml) was heated at 75° C. for 4 h. The mixture was portioned between dichloromethane and 15% aqueous potassium carbonate and the organic solution dried and concentrated. The obtained residue was diluted with methanol (1.5 ml) and reacted with acetic anhydride (1.5 ml) at 50° C. for 2 min and allowed to attend room temperature during 20 min, then pyridine (4 ml) was added and the solution heated again at 50° C. for 3 min, cold and concentrated. The material was purified by silica gel chromatography (light petroleum-ethyl acetate 2:1) to give 95 mg of the subtitle compound.

Provenance & Evidence